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Approved Pro
Approved Pro

CHESAPEAKE ROOFING WINDOWS & SIDING

Roofing, Siding Service, Window Service,

About us

Looking for top-notch roofing, windows, and siding services in Maryland? Look no further than CHESAPEAKE ROOFING WINDOWS & SIDING. With our MHIC LICENSE #126792, we deliver exceptional craftsmanship and customer satisfaction. Contact us today for all your home improvement needs!

Business highlights

Se habla espanol
Family owned & operated
LGBTQ+ Friendly
38 years of experience

Services we offer

ROOFING, WINDOWS, DOORS, VINYL SIDING, HARDIE SIDING, GUTTERS, AND GUTTER GUARDS.

Amenities

Eco Friendly Accreditations

Yes

Free Estimates

Yes

Warranties

Yes

Senior Discount

2%

Accepted Payment Methods

  • Financing Available
  • Check
  • CreditCard
Reviews
4.997 Reviews
Number of StarsImage of DistributionNumber of Ratings
5
98%
4
0%
3
0%
2
0%
1
2%

Filter reviews by service

Showing 26-50 of 97 reviews
Lori B.
Jan 2020
5.0
Roofing, Gutter Repair and Replacement
Yes, I recommend this pro
I had my roof and gutters replaced and they did an awesome job!!! They also were the cheapest estimate I received. I definitely will keep them in mind when replacing my windows.

Karen C.
Jan 2020
5.0
Roofing, Gutter Repair and Replacement
Yes, I recommend this pro
Chesapeake Roofing is prompt, professional, reasonably priced and completed the roof in one day. I was extremely pleased with the end result and I would recommend them to anyone.

Elizabeth A.
Jul 2019
5.0
Roofing
Yes, I recommend this pro
$700
Our dormer on our townhouse roof developed a leak due to faulty sealing to the roof. This caused water to drip into the house and onto the ceiling in one of our bedrooms. We contacted Chesapeake Roofing based upon previous reviews and received a prompt response. We were provided an estimate after submitting photos of the problem and were scheduled. The roofers came on time and were quick to fix the issue. The quote did not change after 5he work was done and we were able to pay online. Highly recommend this company and would definitely hire again for any future roofing needs.

Donna M.
May 2019
5.0
Siding Service, Door Service
Yes, I recommend this pro
$700
Chesapeake Roofing Windows and Siding always does an excellent job for us. We have been using this company for 20+ years and have always been extremely satisfied with their professionalism and the quality of their workmanship.

Jennifer B.
Apr 2019
5.0
Roofing
Yes, I recommend this pro
The experience was wonderful. Mark presented our options after doing a thorough assessment of our issues with the old roof. He did not apply any pressure selling tactics, just let us know what they could offer. He presented a competitive quote and was up-front about fees that may occur during the process. Kurt and his team arrived as scheduled and completed the job on time and cleaned up afterwards. The workers went out of their way to make sure my kids and I could walk safely into and out of the house while they were working. Everyone we came into contact with was very nice. We are not the first ones in our family to use this company and we would gladly refer them to others.

Richard I.
Apr 2019
5.0
Roofing
Yes, I recommend this pro
$10,000
Great! Very happy with work performed, crew and communications with company. Didn't try to sell me extra sheets of plywood after tearing off old roof; and when I had questions, they responded quickly and answered accordingly. Work was done quickly, and they cleaned up well. They'll be on my contact list when I am ready for new windows!

Jamie G.
Mar 2019
5.0
Window Service, Door Service
Yes, I recommend this pro
$5,900
My experience was great. Mark came out for the estimate and provided great customer service. I got 8 windows and a slider glass door in my townhouse. The crew seemed very experienced, provided quality work, and cleaned up after themselves. Would definitely recommend and use them again for other services.

Lou M.
Feb 2019
5.0
Roofing, Siding Service + 1 more
Yes, I recommend this pro
$4,900
The job went very well. Both crews were prompt, courteous and professional. The job site was very clean after the work was completed. I will know if the water problems are resolved after the rain comes in this coming weekend. I would definitely use this company again.

Francis H.
Jan 2019
5.0
Roofing, Siding Service + 2 more
Yes, I recommend this pro
From the time we discussed the work with the marketing person until work was completed, Chesapeake Roofing Windows & Siding was great. Mark helped us with defining the scope of work and suggested both solutions and materials. The price to complete the work was attractive. The work crews arrived at the location when promised and completed the work also as promised. The crews left a clean work site with no damage to other areas of the exterior. The work required a door installation, roof repair, siding installation and aluminum covering of gutter boards and soffits. Seperate crews were provided for each requirement. Excellent workmanship. I will use Chesapeake Roofing again, if, needed and would recommend their services to others.

Bruce C.
Jan 2019
5.0
Roofing
Yes, I recommend this pro
$16,440
Chesapeake's estimator called back less than 24 hours after initial contact and arrived 3 days later to measure the job. He provided the estimate on the spot and next day stopped by with shingle color samples plus addresses of homes with the two shingle colors we were interested in for our roofs. After signing the contract, we were given an approximate install date, which was 3 weeks out. We were promptly informed of a 1 week delay (due to rain) for the install. The crew completed the main house in 2 days ( a Friday and Saturday) and returned early on Monday to complete work on the garage. Aside from a couple of pieces of damaged vinyl siding, the crew was careful to protect shrubs and other plantings adjacent to the main house and garage. Chesapeake sent out their siding crew to replace the damaged vinyl siding. All in all, the project was completed in a timely and professional manner. Of 4 estimates we received, Chesapeak's was the most reasonable.

Dixie R.
Nov 2018
5.0
Roofing
Yes, I recommend this pro
$720
Domenic came out and checked the leak spot, the attic and the overall condition of the roof. He came to the conclusion that it was the ridge vent and that it should be replaced. So far so good. I'm hoping this is the solution to my problem.

John M.
Oct 2018
5.0
Roofing
Yes, I recommend this pro
work was excelant

Patricia D.
Oct 2018
5.0
Roofing, Siding Service + 1 more
Yes, I recommend this pro
We really had a great experience with this company. It came highly recommended to us by others who had various work done. The biggest job was a roof replacement as well as all the gutters, downspouts and covering of wood trim. The pricing was very fair but most importantly, the work was done as agreed and no mysterious upcharges. The second project was railings for a wide cellarway entry. Again, came as scheduled and the project looks great. The last project was miscellaneous siding repair after our deck was replaced. Again, well done. This will always be our go to company for whatever they do that we need. Another benefit it it is a long established local business. They are invested in their reputation and work hard to do excellent work.

Henry K.
Oct 2018
5.0
Roofing
Yes, I recommend this pro
I was worried the day the job was to be done because it was sprinkling rain, but, the crew came out and performed their services with success. They were here for around 9 hours and I haven’t had any issues since. I would highly recommend Chesapeake Roofing to anyone.

Elizabeth S.
Sep 2018
5.0
Roofing
Yes, I recommend this pro
$13,000
A friend recommended this company. Everything went very well from start to finish. Mark the salesperson came to the house and inspected the roof over house and garage. The estimate came on time. Kurt, Mark, and the owner worked with me to make changes to the scope of work and schedule according to my preferences. On installation day, he crew came early and there were plenty of workers to do the job. The crew was there at least 12 hours on a very hot August day. They cleaned up and the yard looked great when the job was finished. All in all, Chesapeake was a great company. I recommended them to my fiance and he had them install a new roof, too!

Vicki J.
Aug 2018
5.0
Roofing
Yes, I recommend this pro
the entire process went very well...from the estimate (came out to do the estimate immediately)...answered all of our questions thoroughly and truthfully. Work was done when and as promised....high quality materials and workmanship. Crew was professional and cleaned everything up as if they had not been there. As soon as the job was completed Domanic stopped by to ensure all had gone as promised.

Barbara W.
Aug 2018
5.0
Roofing
Yes, I recommend this pro
$5,000
This company was very reasonably priced and did a great job. Would recommend them highly.

Emelia S.
Aug 2018
5.0
Roofing
Yes, I recommend this pro
I contacted Chesapeake Roofing, Windows, and Siding about installing a new roof on my townhouse. The estimate I received was actually over $1,000 LESS than what my neighbors paid last year to have their roofs replaced by another local company. I signed the contact but was contacted by my HOA board shortly thereafter who said I needed to change the type of shingle I had put in my contact as it was not the approved shingle type for our community. Chesapeake Roofing, Windows, and Siding told me it was no problem to change the shingle type and quickly drafted me up a new contact to sign. Domenic and Kurt also kept me well informed about when my new roof would be installed as the original date had to be pushed back a few days due to rain. Domenic and his crew cleaned up very well after the roof was installed - my neighbor also told me she was impressed how well they cleaned up. There was a minor issue with some gunk from the gutters that was left on my neighbors siding, however, Kurt responded immediately when I called about this and the debris was power washed clean the next day. I would definitely recommend Chesapeake, Roofing, and Siding to anyone looking to have a new roof installed based on my positive experience!

Lee R.
Jul 2018
5.0
Roofing, Siding Service + 1 more
Yes, I recommend this pro
$775
I got windows from this company 4-5 years ago and the process was so simple and easy, I used them again for wrapping my bay window in PVC. This company came highly recommended to me by friend who have used their services in the past. Both jobs went off without a hitch. I would not have even known they were there except for the new windows and now new beautiful bay window. The owner, Kurt, is so nice and professional and SO easy to deal with. Their quotes for me and my friends have always come in lower than area competition, and the whole process for both jobs was painless and easy! I would HIGHLY HIGHLY recommend this company and do recommend them to my friends and colleagues. I would most definitely use them again should the need arise.

Wayne N.
Jun 2018
5.0
Roofing
Yes, I recommend this pro
$400
Kurt was very prompt and responsive. His roofer did a great job and the shingle replacement also included a visual inspection of the entire roof. Very satisfied.

Patricia H.
May 2018
5.0
Gutter Repair and Replacement
Yes, I recommend this pro
$8,500
An appointment was set up immediately for an estimate. The gentleman arrived promptly and after a discussion of what work I wanted done, he completed a thorough review of my home and then provided a written estimate. Because of my prior research of the company and his professionalism, I felt comfortable signing a contract while he was here. The owner contacted me within 2 days to set a date for installation. The soffit was installed when scheduled and the gutters and downspouts were installed two days later. Installation was flawless and everything looks great. I couldn't be happier as it really needed to be done. I would definitely recommend this contractor and I will use them again if the need arises.

Valerie C.
May 2018
5.0
Roofing
Yes, I recommend this pro
For the past 2 years, we've had patch repairs done on our roof and soffits. While most companies are happy to "upsell" you to death, Kurt was always honest and upfront about what REALLY needed to be done at each repair request, and his prices are fair market value. The workers were punctual and tidy at all times. This spring we finally had to get our roof replacement and I didn't give a second thought to calling Chesapeake (Kurt) for this job. I would highly recommend this company for all of your roofing and siding needs!

Donna M.
Apr 2018
5.0
Siding Service, General Remodeling
Yes, I recommend this pro
$3,000
We have been using Chesapeake Roofing Windows and Siding for 20+ years and have always been extremely satisfied with their professionalism and the quality of their workmanship. We have used all of the services they provide. All of this at the best price available (we get three bids for any work we need). The current job was for repair work to our existing siding and trim, and installation of new columns to our home. The workman were so pleasant and did an outstanding job. The new columns look fabulous.

Andrew D.
Apr 2018
5.0
Roofing
Yes, I recommend this pro
We have used Chesapeake Roofing for over ten years for small repairs to our main residence. They have always responded promptly and performed the repairs professionally. Our son recently purchased an old residence and had all windows replaced, a new roof & siding installed. All work crews were professional.

Patricia W.
Apr 2018
5.0
Roofing, Siding Service + 1 more
Yes, I recommend this pro
Upon the recommendation of a neighbor, we had used Chesapeake to replace roofing and siding in 2003. Owner Kurt even extended our porch and built a new roofline! We were extremely pleased with their work. Since that time we have recommended them to our daughter, who, in turn recommended them to her neighbors. All were equally pleased. When we realized this year that they also do windows, it was a "no-brainer" to contact them for a job estimate. We also received an estimate from a well advertised window company, by the way. That visit was equivalent to talking with a stereotypical used car salesperson! The Chesapeake employee's (Mark) visit was friendly, courteous, and professional. Absolutely no-pressure salesmanship. We really liked the quality of the windows described and shown. We followed up the next week to finalize a contract. Within three weeks thereafter, the windows were installed. The workmen were fast and efficient. Their work was impeccable. They cleaned as they went along, and rechecked everything upon completion. Just as with roofing and siding, we'll be sure to recommend Chesapeake to anyone looking for new windows!
Showing 26-50 of 97

Licensing

Bonded

Insured

Licensed*

Trade License Number

36354

Trade License Locale

Maryland

Trade License Authority

Maryland: General

Trade License Expiration

10/23/2025

State Contractor License Requirements

All statements concerning insurance, licenses, and bonds are informational only, and are self-reported. Since insurance, licenses and bonds can expire and can be cancelled, homeowners should always check such information for themselves. To find more licensing information for your state, visit our Find Licensing Requirements page.

*Contact business to see additional licenses.

FAQ

CHESAPEAKE ROOFING WINDOWS & SIDING is currently rated 4.9 overall out of 5.

Monday: 7:30 AM - 10:00 PM Tuesday: 7:30 AM - 10:00 PM Wednesday: 7:30 AM - 10:00 PM Thursday: 7:30 AM - 10:00 PM Friday: 7:30 AM - 10:00 PM Saturday: 7:30 AM - 10:00 PM Sunday: 7:30 AM - 10:00 PM

CHESAPEAKE ROOFING WINDOWS & SIDING accepts the following forms of payment: Financing Available, Check, CreditCard

Yes, CHESAPEAKE ROOFING WINDOWS & SIDING offers free project estimates.

Yes, CHESAPEAKE ROOFING WINDOWS & SIDING offers eco-friendly accreditations.

Yes, CHESAPEAKE ROOFING WINDOWS & SIDING offers a 2% senior discount.

No, CHESAPEAKE ROOFING WINDOWS & SIDING does not offer emergency services.

Yes, CHESAPEAKE ROOFING WINDOWS & SIDING offers warranties.

CHESAPEAKE ROOFING WINDOWS & SIDING offers the following services: ROOFING, WINDOWS, DOORS, VINYL SIDING, HARDIE SIDING, GUTTERS, AND GUTTER GUARDS.